The ten-year anniversary of the Eastern Partnership agreement offers an excellent opportunity to take stock of past achievements and future challenges. Armenia, Azerbaijan, Belarus, Georgia, Moldova, and Ukraine certainly form a quite heterogeneous group. At the same time, they face certain common political and economic difficulties as their main task for the near future will be the enhancement of their state institutions and economic performance. Nevertheless, the geopolitical location of the region in the middle of the deepening crisis between the West and Russia implies that the pathway of the region is not predetermined. The four potential scenarios for the region’s future show it can vary from cohesion to conflict.